In 1999, Ravikant co-founded consumer product review site Epinions.[8] They raised $45 million in venture capital from Benchmark Capital and August Capital.[8] In 2003, Epinions merged with comparison pricing site Dealtime with the approval of Ravikant and the other co-founders that had left the company—even though it meant valuing their shares at zero.[8]
The merged company became Shopping.com which held an IPO in October 2004.[8] After its first day of trading, it was worth $750 million.[8] In January 2005, Ravikant and three of his co-founders filed a lawsuit against Benchmark, August Capital, their co-founder Nirav Tolia who remained at Epinions after his co-founders' departures claiming that—to get their approval for the merger—they were misled to believe that at the time of the merger, the company was worth "$23 million to $38 million", less than the $45 million that they had raised in outside capital, making their shares worthless. The lawsuit was settled in December 2005.
Hit Forge
Around 2007, Ravikant started a $20 million early stage venture capital fund named "The Hit Forge".[9] Hit Forge invested in prominent startups including Twitter, Uber and Stack Overflow.[10][11][12]
In 2007, Ravikant began co-writing a blog called Venture Hacks, which "offered detailed advice on negotiating term sheets, explained which sections mattered, and which provisions were bogus."[13] That blog evolved into AngelList, which Ravikant co-founded in 2010, as a fundraising platform for startups to raise money from angel investors. AngelList also operates Product Hunt. In 2022, AngelList reached a $4 billion valuation.[14] Naval is the chairman and former CEO of AngelList.[2]
In 2017, Naval launched Spearhead, an investment fund which raised $100m for its third fund to provide founders with $1m each to invest in technology companies as angel investors.[16] The first two classes of Spearhead include founders from 35 companies. Together, these companies are worth over $10B, and four of them are unicorns. The companies include Neuralink, Opendoor, PillPack, Shippo (company), Rippling and Scale.[17] Previous Spearhead leads include Shippo co-founder and chief executive officer Laura Behrens Wu, Scale AI founder and CEO Alexandr Wang and Rippling co-founder and chief technology officer Prasanna Sankar.[17]
With Ravikant's permission, Eric Jorgenson curated Naval's tweets, essays, and interviews on wealth and happiness, then published them as a free downloadable book called The Almanack of Naval Ravikant, with a foreword by Tim Ferriss.[18]
Ravikant has a chapter giving advice in Tim Ferriss' book Tools of Titans.
Airchat
Ravikant co-founded Airchat in 2023, a social media app.[19] It uses Generative AI and is similar to Instagram stories.[19]